Synthesis of substituted tetrahydrofurans via intermolecular reactions of γ-chlorocarbanions of 3-substituted 3-chloro-propylphenyl sulfones with aldehydes

被引：6

作者：

Brandt, Agnieszka ^{[1
,2
]}

Wojtasiewicz, Anna ^{[1
]}

Sniezek, Marcin ^{[1
]}

Makosza, Mieczyslaw ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw 42, Poland

[2] Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany

来源：

TETRAHEDRON | 2010年 / 66卷 / 18期

关键词：

Carbanions; Aldol reaction; Cyclization; STEREOSELECTIVE-SYNTHESIS;

D O I：

10.1016/j.tet.2010.02.006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Carbanions of 3-substituted-3-chloropropyl phenyl sulfones add to carbonyl groups of aldehydes to produce aldol type adducts that undergo 1,5-intramolecular substitution giving 2,3,5-trisubstituted tetrahydrofurans. The effect of substituents in the 3-position of these sulfones on the relative rates of 1,3-intramolecular substitution of the corresponding gamma-chlorocarbanions and their intramolecular addition are disclosed. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：3378 / 3385

页数：8

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